Dipivefrin hydrochloride

Base Information

• Chemical Name: Dipivefrin hydrochloride
• CAS No.: 64019-93-8
• Molecular Formula: C₁₉H₂₉NO₅*ClH
• Molecular Weight: 387.904
• Hs Code.: 2922504500
• European Community (EC) Number: 264-609-5
• UNII: 5QTH9UHV0K
• DSSTox Substance ID: DTXSID2045494
• Wikidata: Q27106427
• NCI Thesaurus Code: C47495
• ChEMBL ID: CHEMBL1200833
• Mol file: 64019-93-8.mol

Synonyms:(+)-dipivefrin;(-)-dipivefrin;(R)-dipivefrine;(RS)-4-(1-hydroxy-2-(methylamino)ethyl)-O-phenylene dipivalate hydrochloride;(S)-dipivefrin;(S)-dipivefrine;adrenaline dipivalate;Akpro;Apo-Dipivefrin;d Epifrin;Diopine;dipivaloylepinephrine;dipivalyl epinephrine;dipivefrin;dipivefrin acetate, (+-)-isomer;dipivefrin citrate (1:1), (+-)-isomer;dipivefrin HCl;dipivefrin hydrochloride;dipivefrin hydrochloride, (+-)-isomer;dipivefrin hydrochloride, (R)-;dipivefrin hydrochloride, (S)-;dipivefrin monophosphate, (+-)-isomer;dipivefrin monosulfate, (+-)-isomer;dipivefrin nitrate, (+-)-isomer;dipivefrin perchlorate;dipivefrin propanoate, (+-)-isomer;dipivefrin tartrate (1:1), (+-)-(R-(R*,R*))-isomer;dipivefrin tartrate (1:1), (R)-(R-(R*,R*))-isomer;dipivefrin, (R)-isomer;dipivefrine;dipivefrine hydrochloride;dipivefrine hydrochloride, (R)-;dipivefrine hydrochloride, (S)-;dipivefrine, (R)-;Dipoquin;Glaucothil;Glaudrops;PMS-Dipivefrin;propanoic acid, 2,2-dimethyl-, 4-(1-hydroxy-2-(methylamino)ethyl)-1,2-phenylene ester, (+-)-;propanoic acid, 2,2-dimethyl-, 4-(1-hydroxy-2-(methylamino)ethyl)-1,2-phenylene ester, (R)-;propanoic acid, 2,2-dimethyl-, 4-(1-hydroxy-2-(methylamino)ethyl)-1,2-phenylene ester, (S)-;Propine;ratio-Dipivefrin

Chemical Property of Dipivefrin hydrochloride

Chemical Property:

• Vapor Pressure: 8.89E-10mmHg at 25°C
• Melting Point: 158-159°
• Boiling Point: 473.7 °C at 760 mmHg
• PKA: 8.40(at 25℃)
• Flash Point: 240.3 °C
• PSA: 84.86000
• LogP: 4.03530
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Freely soluble in water, very soluble in methanol, freely soluble in ethanol (96 per cent) and in methylene chloride.
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 387.1812508
• Heavy Atom Count: 26
• Complexity: 463

Purity/Quality:

99.9% ^*data from raw suppliers

Dipivefrine hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)C(=O)OC1=C(C=C(C=C1)C(CNC)O)OC(=O)C(C)(C)C.Cl
• Description: Dipivefrin hydrochloride is an antiglaucoma prothrombotic drug that is hydrolyzed to its active compound epinephrine by esterases in the cornea.
• Uses: Dipivefrine Hydrochloride acts as an anti-glaucoma agent. Adrenergic (ophthalmic)

Technology Process of Dipivefrin hydrochloride

There total 12 articles about Dipivefrin hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(R)-2-(N-benzyl-N-methylamino)-1-<3',4'-bis<(pivaloyl)oxy>phenyl>ethan-1-ol (133789-72-7) → (-)-(R)-3,4-di-O-pivaloylepinephrine hydrochloride (79071-01-5,64019-93-8)

Guidance literature:

With hydrogenchloride; palladium on activated charcoal; In ethanol; under 11400 Torr; Yield given;

DOI:10.1002/hlca.19910740216

Reference yield:

(R)-2-(N-benzyl-N-methylamino)-1-<3',4'-bis<(pivaloyl)oxy>phenyl>ethan-1-ol (133789-72-7) → (+)-(S)-3,4-di-O-pivaloylepinephrine hydrochloride (133815-41-5,64019-93-8) + (-)-(R)-3,4-di-O-pivaloylepinephrine hydrochloride (79071-01-5,64019-93-8)

Guidance literature:

With hydrogenchloride; palladium on activated charcoal; In ethanol; under 11400 Torr; Yield given. Yields of byproduct given;

DOI:10.1002/hlca.19910740216

Reference yield:

(R)-2-(N-benzyl-N-methylamino)-1-<3',4'-bis<(pivaloyl)oxy>phenyl>ethan-1-ol (133789-72-7) → (+)-(S)-3,4-di-O-pivaloylepinephrine hydrochloride (133815-41-5,64019-93-8) + (-)-(R)-3,4-di-O-pivaloylepinephrine hydrochloride (79071-01-5,64019-93-8)

Guidance literature:

With hydrogenchloride; palladium on activated charcoal; In ethanol; under 11400 Torr; Yield given. Yields of byproduct given;

DOI:10.1002/hlca.19910740216

upstream raw materials:

(R)-2-(N-benzyl-N-methylamino)-1-<3',4'-bis<(pivaloyl)oxy>phenyl>ethan-1-ol

pivaloyl chloride

4-formyl-1,2-phenylene bis(2,2-dimethylpropanoate)

(R)-1-<3',4'-bis<(pivaloyl)oxy>phenyl>-2-(p-tolylsulfinyl)ethan-1-on

Refernces

• 1、 Solladie-Cavallo,Simon-Wermeister,Farkhani. "Enanthioselective synthesis of both enantioners of a isoproterenol analogue and of di-O-pivaloylepinephrine". . p. 390 - 396. Retrieved 2007/10/02.